4-Quinolinecarboxylic acid → 4-Quinolinecarbonyl chloride

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([Cl:16])=[O:13])=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 102434-Quinolinecarboxylic acid

HCID 24386Thionyl Chloride

Product 1

HCID 99901264-Quinolinecarbonyl chloride

Procedure

A solution of 4-quinolinecarboxylic acid (Aldrich, 0.25 g, 1.4 mmol) in 5 mL of thionyl chloride was warmed to reflux and allowed to stir for 1 hour. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. This material was dissolved in 10 mL toluene and concentrated under reduced pressure (3×) to afford the title compound.

Workup

temperatureto reflux
concentrationconcentrated under reduced pressure
dissolutionThis material was dissolved in 10 mL toluene
concentrationconcentrated under reduced pressure (3×)

Sources & evidence

ORD record: ord-cdafd995a22746e6b7c3dd5a072b0f2f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Reaction notes

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